Home Other Building Blocks (S)-2-Amino-3-(5-fluoro-1h-indol-3-yl)propanoic acid

(S)-2-Amino-3-(5-fluoro-1h-indol-3-yl)propanoic acid

CAS No.:
16626-02-1
Catalog Number:
AG001WLJ
Molecular Formula:
C11H11FN2O2
Molecular Weight:
222.2156
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Product Description
Catalog Number:
AG001WLJ
Chemical Name:
(S)-2-Amino-3-(5-fluoro-1h-indol-3-yl)propanoic acid
CAS Number:
16626-02-1
Molecular Formula:
C11H11FN2O2
Molecular Weight:
222.2156
MDL Number:
MFCD00066470
IUPAC Name:
(2S)-2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid
InChI:
InChI=1S/C11H11FN2O2/c12-7-1-2-10-8(4-7)6(5-14-10)3-9(13)11(15)16/h1-2,4-5,9,14H,3,13H2,(H,15,16)/t9-/m0/s1
InChI Key:
INPQIVHQSQUEAJ-VIFPVBQESA-N
SMILES:
N[C@H](C(=O)O)Cc1c[nH]c2c1cc(F)cc2
UNII:
17H03VO4KZ
Properties
Complexity:
275  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
222.08g/mol
Formal Charge:
0
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
222.219g/mol
Monoisotopic Mass:
222.08g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
79.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.7  
Literature
Title Journal
Effect of juxtamembrane tryptophans on the immersion depth of Synaptobrevin, an integral vesicle membrane protein. Biochimica et biophysica acta 20121201
Specific fluorine labeling of the HyHEL10 antibody affects antigen binding and dynamics. Biochemistry 20120731
Structural investigation of the transmembrane C domain of the mannitol permease from Escherichia coli using 5-FTrp fluorescence spectroscopy. Biochimica et biophysica acta 20120301
5-fluoro-D,L-tryptophan as a dual NMR and fluorescent probe of α-synuclein. Methods in molecular biology (Clifton, N.J.) 20120101
Reduced fluorescence lifetime heterogeneity of 5-fluorotryptophan in comparison to tryptophan in proteins: implication for resonance energy transfer experiments. The journal of physical chemistry. B 20110609
Residue-specific global fluorination of Candida antarctica lipase B in Pichia pastoris. Molecular bioSystems 20100901
Localization of the substrate-binding site in the homodimeric mannitol transporter, EIImtl, of Escherichia coli. The Journal of biological chemistry 20100813
5-fluorotryptophan as dual probe for ground-state heterogeneity and excited-state dynamics in apoflavodoxin. FEBS letters 20090903
Structure of the cytoplasmic loop between putative helices II and III of the mannitol permease of Escherichia coli: a tryptophan and 5-fluorotryptophan spectroscopy study. Biochemistry 20090616
Substrate promiscuity of the cyclic dipeptide prenyltransferases from Aspergillus fumigatus ( section sign). Journal of natural products 20090101
A convenient one-step synthesis of L-aminotryptophans and improved synthesis of 5-fluorotryptophan. Bioorganic & medicinal chemistry letters 20080815
Auxotrophic-precursor directed biosynthesis of nonribosomal lipopeptides with modified tryptophan residues. Organic & biomolecular chemistry 20080321
Lactococcus lactis as expression host for the biosynthetic incorporation of tryptophan analogues into recombinant proteins. The Biochemical journal 20080101
YddG from Escherichia coli promotes export of aromatic amino acids. FEMS microbiology letters 20071001
Determination of the 19F NMR chemical shielding tensor and crystal structure of 5-fluoro-dl-tryptophan. Journal of magnetic resonance (San Diego, Calif. : 1997) 20070701
Nanosecond relaxation dynamics of protein GB1 identified by the time-dependent red shift in the fluorescence of tryptophan and 5-fluorotryptophan. The journal of physical chemistry. B 20061228
Hydrophobic effect and hydrogen bonds account for the improved activity of a complement inhibitor, compstatin. Journal of medicinal chemistry 20060727
Molecular and biochemical studies of chondramide formation-highly cytotoxic natural products from Chondromyces crocatus Cm c5. Chemistry & biology 20060601
Alpha-synuclein structures probed by 5-fluorotryptophan fluorescence and 19F NMR spectroscopy. The journal of physical chemistry. B 20060406
In vivo and in vitro studies of Chlamydia trachomatis TrpR:DNA interactions. Molecular microbiology 20060301
Sensitive high-performance liquid chromatographic assay for D-amino-acid oxidase activity in mammalian tissues using a fluorescent non-natural substrate, 5-fluoro-D-tryptophan. Journal of chromatography. A 20060217
A 1H/19F minicoil NMR probe for solid-state NMR: application to 5-fluoroindoles. Journal of magnetic resonance (San Diego, Calif. : 1997) 20060101
Effects of Phe-to-Trp mutation and fluorotryptophan incorporation on the solution structure of cardiac troponin C, and analysis of its suitability as a potential probe for in situ NMR studies. Protein science : a publication of the Protein Society 20050901
Ionization potentials of fluoroindoles and the origin of nonexponential tryptophan fluorescence decay in proteins. Journal of the American Chemical Society 20050323
Interaction of the eukaryotic pore-forming cytolysin equinatoxin II with model membranes: 19F NMR studies. Journal of molecular biology 20050318
Static and time-resolved fluorescence investigations of tryptophan analogues--a solvent study. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20040401
19F NMR studies of plasminogen activator inhibitor-1. Biochemistry 20040217
In vivo synthesized proteins with monoexponential fluorescence decay kinetics. Journal of the American Chemical Society 20040114
(19)F NMR studies of the leucine-isoleucine-valine binding protein: evidence that a closed conformation exists in solution. Journal of biomolecular structure & dynamics 20031001
Regulation of tryptophan synthase gene expression in Chlamydia trachomatis. Molecular microbiology 20030901
Use of intein-directed peptide biosynthesis to improve serum stability and bioactivity of a gelatinase inhibitory peptide. Combinatorial chemistry & high throughput screening 20030201
[5-fluoro-tryptophan-containing N-terminal domain of the alpha-subunit of the Torpedo californica acetylcholine receptor: preparation in E. coli and 19F NMR study]. Bioorganicheskaia khimiia 20030101
Evolution of phage with chemically ambiguous proteomes. BMC evolutionary biology 20030101
19F NMR study of the leucine-specific binding protein of Escherichia coli: mutagenesis and assignment of the 5-fluorotryptophan-labeled residues. Protein engineering 20021101
Role of entropy in protein thermostability: folding kinetics of a hyperthermophilic cold shock protein at high temperatures using 19F NMR. Biochemistry 20021001
Protein-protein interaction using tryptophan analogues: novel spectroscopic probes for toxin-elongation factor-2 interactions. Biochemistry 20010828
Solution-state NMR investigations of triosephosphate isomerase active site loop motion: ligand release in relation to active site loop dynamics. Journal of molecular biology 20010629
Production, isolation and structure determination of novel fluoroindolocarbazoles from Saccharothrix aerocolonigenes ATCC 39243. The Journal of antibiotics 20010101
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